Methyl Acrylate → HCID 19854194, compound

HRID 1649626Notes

Reaction equation

HRID 1649626 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[C:13](OC)(=[O:16])[CH:14]=[CH2:15].C[O-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:11][C:10]2=[O:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 10942334Sodium Methoxide

Product 1

HCID 19854194HCID 19854194, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 4-methoxyphenylacetone (50 g) and methyl acrylate (26.2 g) was added dropwise to a stirred suspension of sodium methoxide (from 7.5 g sodium in 50 ml methanol) in dry xylene (160 ml) at ambient temperature. The resulting solution was then refluxed for 3 hours. The xylene was evaporated in vacuo and the residue partitioned between water and diethyl ether. The aqueous phase was further extracted with diethyl ether. The aqueous layer was finally acidified with concentrated hydrochloric acid to precipitate 4-(4-methoxyphenyl)cyclohexane-1,3-dione (37 g) as a white solid (after an ether washing) of m.p. 150°-151° C.

Workup

  1. temperatureThe resulting solution was then refluxed for 3 hours
  2. customThe xylene was evaporated in vacuo
  3. customthe residue partitioned between water and diethyl ether
  4. extractionThe aqueous phase was further extracted with diethyl ether
  5. customto precipitate 4-(4-methoxyphenyl)cyclohexane-1,3-dione (37 g) as a white solid (after an ether washing) of m.p. 150°-151° C.

Sources & evidence

ORD record
ord-31e3ea61c4ae4545b1a133128dec7a02
Source dataset
uspto-grants-1990_05
Patent number
US04921524

Reaction notes

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